Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

• Shyam Sathyamoorthi,
• Appasaheb K. Nirpal,
• Dnyaneshwar A. Gorve and
• Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

• : alkene; amino-sulfonoxylation; metal-free; tethered nitrenium; Introduction Our laboratory has a programmatic focus on the development of metal-free oxidation reactions that avoid the use of toxic reagents such as osmium and chromium [1][2][3]. In line with this agenda, we recently explored a mild amino

Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)

• Morifumi Fujita,
• Koki Miura and
• Takashi Sugimura

Beilstein J. Org. Chem. 2018, 14, 659–663, doi:10.3762/bjoc.14.53

• )-isomer. Keywords: 1,2-difunctionalization of alkenes; enantioselective synthesis; hypervalent iodine; oxidation; Findings Hypervalent aryl-λ3-iodanes have been widely used for metal-free oxidation with high selectivity in organic synthesis [1][2][3]. The reactivity of an aryl-λ3-iodane is controlled by

Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides

• Long-Yi Xi,
• Ruo-Yi Zhang,
• Lei Shi,
• Shan-Yong Chen and
• Xiao-Qi Yu

Beilstein J. Org. Chem. 2016, 12, 1072–1078, doi:10.3762/bjoc.12.101

• described. A range of electronically diverse acetophenones reacted well with several 2-aminobenzenesulfonamides, affording 3-acylbenzothiadiazine 1,1-dioxides in good yields. Keywords: 3-acylbenzothiadiazine 1,1-dioxides; cyclization; metal-free; oxidation; Introduction Benzothiadiazine 1,1-dioxide

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• hydrogen abstraction from NHPI, leading to the generation of PINO. This approach was successfully applied to promote the visible-light-induced metal-free oxidation of allylic substrates (Scheme 23). Other initiators In their ongoing research dedicated to NHPI activation towards the aerobic oxidation of

• derivatives. The scope of the reaction was investigated and its applicability was extended to different C–H bonds, including benzylic, propargylic, and aliphatic ones. Furthermore, the hydrazine compounds were readily converted to the corresponding carbamates and amines. Conclusion Metal-free oxidation

• from N-alkoxyphthalimides. Visible-light/g-C3N4 induced metal-free oxidation of allylic substrates. NHPI/o-phenanthroline-mediated organocatalytic system. NHPI/DMG-mediated organocatalytic system. NHPI catalyzed oxidative cleavage of C=C bonds. Synthesis of hydrazine derivatives. Acknowledgements We

NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes

• Lennart Möhlmann,
• Stefan Ludwig and
• Siegfried Blechert

Beilstein J. Org. Chem. 2013, 9, 602–607, doi:10.3762/bjoc.9.65

• -free oxidation; N-heterocyclic carbene; organocatalysis; Introduction The development of efficient and selective aerobic oxidation methods for organic substrates is of increasing interest and an attractive goal in green chemistry [1][2][3]. In a recent communication we reported on selective oxidation

• of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent. Keywords: aerobic oxidation; chemoselective oxidation; metal